反应详情

Combine 4-bromoanisole (19.6 g, 104 mmol), cyclohexanone (13.2 g, 136 mmol), sodium tert-butoxide (11.8 g, 120 mmol), palladium acetate (0.47 g, 2.1 mmol), (oxy-di-2,1-phenylene)bis-diphenylphosphine (2.28 g, 4.1 mmol) and toluene (240 mL) and heated at 90° C. under nitrogen. After 18 hours, cool to room temperature and add 1N HCl (120 mL). Extract with methylene chloride and wash the combined extracts with brine. Dry the organic layer over sodium sulfate and concentrate in vacuo. Purify by flash chromatography using silica gel and 10% ethyl acetate-hexanes to yield the titled compound (8.15 g, 38%) as a white solid. 1H NMR (CDCl3) δ 7.12 (d, 2H, J=7.5 Hz), 6.92 (d, 2H, J=7.5 Hz), 3.84 (s, 3 H), 3.59 (dd, 1H, J=8.0 and 3.5 Hz), 2.60-2.45 (m, 2H), 2.29 (m, 1H), 2.18 (m, 1H), 2.04 (m, 2H), 1.85 (m, 2H). MS m/z 205 (M+1).

1. extractionExtract with methylene chloride
2. washwash the combined extracts with brine
3. dry with materialDry the organic layer over sodium sulfate
4. concentrationconcentrate in vacuo
5. customPurify by flash chromatography